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Wander Off the Beaten Path

By Hilary DelRoss

Originally published in the 2018 Ski Vermont magazine

Wander Off the Beaten PathThe routes that connect Vermont’s ski areas are rich with fascinating history and captivating culture. As you drive through the Green Mountain State during a winter ski trip, we invite your crew to put down the tech and weave some of Vermont’s local ski story into your family vacation with this guide to historical landmarks and cultural pit stops waiting just outside your car windows. See how many you can find on your next road trip — we’ll even provide snacks.

As the No. 1 ski and snowboard state in the East, you know you’re in for an epic alpine adventure when you arrive at Vermont’s ski and snowboard resorts, but what you may not realize is the picturesque steeples, covered bridges and pastoral landscapes you whiz by on your way to the slopes are more than mile markers; they are the icons that give us a peek into the past. Vermont’s local culture is steeped in rich history, beautiful architecture and diverse arts found throughout its mountain communities, many of which are located along the scenic routes leading to and from ski and snowboard resorts.

Here are a few favorite landmarks that link the local vibe and nearby slopes, revealing hints of what life was like for some of the state’s earliest skiers. When planning your upcoming Vermont ski trip, we invite you to explore these and other treasures lying just off the beaten path.

Northern Vermont

Popping up where country roads cross over winding waterways, covered bridges are quintessentially Vermont, as our state boasts the highest concentration of these structures in New England. Bridges were designed with covers to protect the bridge from damage caused by winter elements because the covers could be more easily repaired or replaced than the bridges themselves. They get their charming appeal from the many types of construction and architectural features used to build them, and two different examples can be found on a short detour in Lyndonville, on your way to Burke Mountain and Jay Peak Resort.

Covered Bridge Vermont

The Old Schoolhouse Covered Bridge (South Wheelock Road) was built in 1879 and was listed in the National Register of Historic Places in 1974. The road has since been rerouted around the bridge so you can’t drive through it, but you can park nearby to get a closer look. This bridge is very photogenic with arched covered walkways on either side protected by an extended roofline — unique features for its time, and the only bridge of its kind still standing in Vermont. Imagine early model cars puttering past kids dressed in bundles of wool outer layers shuffling through the snow on their way to school. Then, buckle up and continue your covered bridge tour by looping back over the South Wheelock Branch of the Passumpsic River, a small tributary of the Connecticut River, via the Chamberlin Mill Covered Bridge. Before you continue north, make a half-mile loop to the west and drive your car through this bridge, which was built in 1881 and is also listed on the National Register of Historic Places.

In communities where skiing families came to settle down, their ski kids needed a place to learn during the school year. Sometimes one-room, and sometimes larger, schoolhouses historically served as community gathering spaces when class was not in session. While driving through historic districts en route to ski areas like Smugglers’ Notch Resort or Bolton Valley keep your eyes peeled for these utilitarian structures.

Today, three historic schoolhouses in Stowe (School Street) are open to the public and showcase artifacts, art and literature, much of it related to the community’s history. Currently home to the Stowe Historical Society, the Helen Day Art Center and Stowe Library, each of these former schools, offer a look at what local life was like at the base of nearby Stowe Mountain Resort. View decades-old photos and postcards featuring citizens, buildings and the landscape — the plow trucks didn’t quite look the same back then. See how local artists interpret the world through a rotating selection of indoor and outdoor exhibits; or create your own works of art — classes are available for any abilities and all ages, even art birthday parties.

Vermont Ski & Snowboard Museum

Stowe also boasts some of the country’s oldest ski history, which includes its claim as the 1938 birthplace of the National Ski Patrol. The Vermont Ski and Snowboard Museum (South Main Street) collects, preserves and displays pieces that you can envision yourself riding, wearing and training in: retro ski equipment and lift technology, ski fashion throughout the last century, memorabilia recognizing the 10th Mountain Division’s on-snow contributions in World War II and mementos from Olympic athletes with Vermont ties. Bring home a retro ski poster to adorn the walls of your home and don’t miss the Nordic-inspired sculpture just outside the museum’s front doors, made of a collection of 40 cross-country skis from the 1970s and ’80s arranged in a helical spiral.

Central Vermont

Vermont Route 100 was built in 1940 following the valleys of the Green Mountains and is now often referred to as the Skiers Highway because it connects most resorts in the state. From Stowe, cruise south to the stretch of this road in Moretown and Waitsfield that takes you to Mad River Glen and Sugarbush Resort, and you’ll see an expanse of fertile farmland along the banks of the Mad River. Ask every passenger in the car to look out their window, and they’ll each get a different view of the collection of farmsteads that make up the Mad River Valley Rural Historic District. Imagine life on these properties, which have been around since the 1700s, and what it was like to work in the barns and live in the homesteads that sprawled from the base of the Green Mountains to the west and the Northfield Mountains to the east. The valley has a rich agricultural history and relics here demonstrate an evolution in farming traditions and technology over time. Notice the Gothic Revival–style farmhouses among large multipurpose barns that replaced small, task-oriented workspaces; silos were made of wood, then cement, then metal; maple sugarhouses with wood-fired evaporators wait for sap to flow from sugarbushes laced with plastic tubing; and mills processed wood, grain and fiber as local needs fluctuated. Farms here still produce wool, meat, dairy and maple syrup — try to identify just how many different agricultural products are available the next time you drive this route.

Lareau Farm, Vermont

Toward the southern end of the Mad River Valley in Waitsfield, the Inn at Lareau Farm (Lareau Road) is on the National Register of Historic Places. Settled in 1795, Lareau Farm was the home of the valley’s first physician. It contains a classic farmhouse, now a country inn; a rustic, yet recently restored 18th-century barn; and former dairy barn, which is now home of the original American Flatbread. Tuck into this cozy eatery after a day on the slopes and join the celebration of farm-to-table cuisine. Many ingredients come from the surrounding fields and farms, including the greens and cheese in the Evolution salad. Flatbread pizzas are baked in an earthen, wood-fired oven in the middle of the casual, post-and-beam dining room. While you wait for your table (and it’s well worth the wait), visit the bartender for a local favorite, like Lawson’s Sip of Sunshine or family-friendly Rookie’s root beer, let the glow of the outdoor fire pit warm you, and take in the views of the surrounding meadows, woods and river.

Hubbard Cabin Vermont

From Route 100, motor west, up and over Middlebury Gap (Vermont Route 125) to Middlebury College Snow Bowl and Hubbard Cabin. This log cabin dates back to 1938, when it was built by the Civilian Conservation Corps (a work program established by President Franklin D. Roosevelt during the Great Depression) alongside local residents. The Hubbard Cabin was constructed with trees cut from the Snow Bowl’s first ski trails and became one of the earliest base lodges in the country. It’s now one of the oldest base lodges still in use, and you can find it at the back of the ski area parking lot. When the current base lodge was completed in 1962, the cabin transitioned to a caretaker’s residence before falling into disrepair. A local ski club renovated the cabin and began using it as their warming hut after ceremoniously naming it for the college’s first ski coach and Snow Bowl advocate, Richard “Dick” Hubbard.

Continue west to Middlebury College’s Bread Loaf campus in Ripton. Bread Loaf is home to more than 55 kilometers of groomed trails where you can cross-country ski, fat bike or snowshoe at Rikert Nordic Center. You’ll immediately notice the centerpiece of this campus, the Bread Loaf Inn, where Pulitzer Prize–winning poet Robert Frost first attended Middlebury’s annual writers conference in 1938. Frost fell in love with the location, bought some property and returned each year until his death in 1963. The Robert Frost Cabin and Farm is a National Historic Site maintained by the college, and Rikert’s ski trails will take you right past his retreat in the Green Mountain National Forest.

While some of Vermont’s earliest transplants retreated into the quiet of the woods, other residents sought a more social atmosphere. General stores have been a hub of social exchange and commerce in Vermont towns for more than a century, and their doors are open to townies and tourists alike. All walks of life duck into general stores, leading to some interesting opportunities for eavesdropping and people-watching. Step inside and find just about anything you could possibly need: grab a sandwich and fishing bait, or pick up some penny candy and a freshly baked pie, don’t forget new work gloves and a coffee — the possibilities are endless.

Pittsfield General Store Vermont

If you’re heading to Killington Resort, Pico Mountain, Okemo Mountain Resort, Suicide Six or Quechee Ski Area, you’re in luck because you’ll be surrounded by some of Vermont’s longest standing, family-owned general stores. The Original General Store in Pittsfield (Vermont Route 100) is a great stop for pre-ski breakfast. F.H. Gilingham & Sons General Store has remained in its location in the center of historic Woodstock (Elm Street) since 1886. Vermont’s oldest, the Barnard General Store (Vermont Route 12), was saved by local fundraising efforts to keep it from closing. Singleton’s General Store in Proctorsville (Main Street) carries so much more than the “whiskey guns ammo” sign at its entrance would lead you to believe. In Norwich, the motto at Dan & Whit’s General Store (Main Street) speaks for them all: “If we don’t have it, you don’t need it.”

Speaking of families, a short detour while you’re in the area will provide you with a glimpse into what could arguably be one of the most closely-knit communities in Vermont. Head to the top of Plymouth Notch (Vermont Route 100A) where almost every structure in the village is incorporated into the President Calvin Coolidge State Historic Site. This is the birthplace of the 13th U.S. president and Coolidge-family homestead. Take a walk through the 19th-century village during any time of year, and you’ll see the clapboard homes, schoolhouse, general store, church, barns and cheese factory primarily occupied by President Coolidge and seven generations of his family. It was in the parlor of his boyhood home, after news arrived of the death of the 29th U.S. president, Warren G. Harding, that Coolidge took the oath office in an impromptu inauguration performed by his father who was a notary public. The ceremony took place by the light of a kerosene lamp because his father refused to incorporate modern conveniences such as electricity. President Coolidge’s father started the Plymouth Artisan Cheese company on site in 1890, making it the second-oldest cheesemaking operation in the country. The cheese factory follows the same standards and process today as it did under the direction of the Coolidge family, which ran the factory until 1998. It’s open year-round, so be sure to stop in and taste their rich cow’s milk cheeses.

Southern Vermont

For more presidential ties in Vermont, albeit far more lavish, take a self-guided driving tour of the historic mansions in Manchester. The designs of these houses offer a sneak peek into the lives of their past residents. Architectural styles were chosen based on distinct uses, desired aesthetics and materials available at the time of construction. Abraham Lincoln’s son, Robert, built a Georgian Revival–style mansion here after falling in love with the area during family vacations with his mom to the nearby Equinox Resort. He called his estate Hildene (Hildene Road), and it later became home to three generations of the president’s descendants. Robert also served as president of the Pullman Company and, at that time, employed the largest number of African Americans in the county as Pullman porters. Tour the property from its cross-country ski and snowshoe trails, and don’t miss the restored Pullman train car to learn about the porters’ work and how it influenced their lives. Head next door to one of the oldest standing buildings in Manchester, the Inn at Ormsby Hill (Vermont Route 7A). The 1764 structure still contains one of the earliest jail cells in town, which was constructed almost entirely of locally available white marble, as was the inn’s oversized threshold. This was once the home of Robert Isham, a friend and colleague of Robert Todd Lincoln, who later bought the adjacent property where he built Hildene.


The mansions of Manchester stand at the foothills of the Taconic Mountains,located west of the area known as “The Golden Triangle.” The triangle is anchored by Bromley Mountain, Magic Mountain and Stratton Mountain Resort at the corners, and from any one mountain summit, you can see spectacular views of the others. While the ski areas are only a short drive apart, the area between them includes eight towns and villages that have also retained much of their historical flavor, albeit less opulent than those found in Manchester Village. At the heart of Manchester, the lavish Equinox Resort (Union Street) was named after the tallest peak in the Taconic range and is on the National Register of Historic Places, where it is identified as “one of Vermont’s last great 19th-century resort hotels still standing.” Since the Revolutionary War, it has seen numerous changes, including the addition of its trademark fluted columns spanning 285 feet across the façade, which, in conjunction with its neighboring structures, stunningly frames the town square.

See another example of this region’s affluent design just 20 miles south in Bennington’s 35-room Park-McCullough House (Park Street). One of the most well preserved Victorian mansions in the Northeast, this European-style “country house” was built in 1864 using French Second Empire architectural design and Romantic Revival–style details, both of which were on trend for those wealthy enough to build a mansion during the end of the 19th century — in this case, the family’s cash came from the gold rush. It is listed on the National Register of Historic Places and has remained true to its original ornate design while being family occupied for 100 years. One of the family descendants did make renovations to the dining room in anticipation of entertaining the 23rd U.S. president, Benjamin Harrison, who visited for the dedication of the Bennington Battle Monument in 1891.

Battle of Bennington Monument Vermont

If you’re then heading to Mount Snow Resort from the west, you can’t miss the towering Bennington Battle Monument (Monument Circle). The monument is Vermont’s tallest structure at 306 feet and was erected to commemorate the 1777 Battle of Bennington, which became a turning point in the Revolutionary War. This popular state historic site was constructed with locally quarried stone and serves as the unofficial gateway to Vermont’s marble-rich region. The elevator to the top of the monument is closed through the winter, but if you visit for spring skiing at the end of April or beginning of May, you’ll be able to catch a lift and take in views of the underlying landscape in Vermont, Massachusetts and New York.

Explore Further

After reading about all the types of icons and landmarks located across Vermont, and the people who built and used them throughout the state’s history, you might feel like you’ve been on a whirlwind sightseeing tour. While a wealth of sights certainly are out there for you to see, and most are managed by groups of history buffs who are happy to share their knowledge if you stop in to visit, many can be appreciated from the comfort of your car as you dart across the state in search of fresh tracks. Explore a different route the next time you head to the slopes or just try to look at your normal route in a new light. However you get there, be sure to keep your eyes open because sometimes that’s all the effort it takes to discover something new in between base areas. It’s these little discoveries that help make Vermont such a special place to visit.


Special thanks to Vermont’s Department of Tourism & Marketing and Division for Historic Preservation for these suggestions. To discover even more artistic, cultural and historic attractions while traveling to and from the slopes, visit and


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